Water → (4S)-2,2-Dimethyl-4-(4-cyanophenoxy)methyl-1,3-dioxolane

Temperature

110 °C

A solution of 4-hydroxy benzonitrile (55 g) in methanol (100 ml) was treated with potassium hydroxide (29 g) in water (30 ml) and evaporated at reduced pressure. The remaining potassium salt was dissolved in dry dimethylformamide (75 ml) and (4R)-2,2-dimethyl-4 - methanesulfonyloxymethyl-1,3-dioxolane, 82.2 g, was add stirring at 110° C. for 20 h, allowed to cool and distributed between ether and water. The aqueous phase was extracted three times with ether, the combined ether phases washed three times with 10% aqueous potassium hydroxide and twice with water, dried over anhydrous sodium sulfate and evaporated. Yield 77 g of the title compound.

1. customevaporated at reduced pressure
2. dissolutionThe remaining potassium salt was dissolved in dry dimethylformamide (75 ml)
3. addition(4R)-2,2-dimethyl-4 - methanesulfonyloxymethyl-1,3-dioxolane, 82.2 g, was add
4. temperatureto cool
5. extractionThe aqueous phase was extracted three times with ether
6. washthe combined ether phases washed three times with 10% aqueous potassium hydroxide
7. dry with materialtwice with water, dried over anhydrous sodium sulfate
8. customevaporated

ORD record

ord-104d16223d4a4b9ca9b898b2d5970fa2

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05155133